(4S,5R)-2,2-diethyl 4-methyl 4-(4-bromo-2-nitrophenyl)-5-phenylpyrrolidine-2,2,4-tricarboxylate

Base Information

• Chemical Name: (4S,5R)-2,2-diethyl 4-methyl 4-(4-bromo-2-nitrophenyl)-5-phenylpyrrolidine-2,2,4-tricarboxylate
• CAS No.: 1291104-18-1
• Molecular Formula: C₂₄H₂₅BrN₂O₈
• Molecular Weight: 549.375
• Mol file: 1291104-18-1.mol

Synonyms:(4S,5R)-2,2-diethyl 4-methyl 4-(4-bromo-2-nitrophenyl)-5-phenylpyrrolidine-2,2,4-tricarboxylate

Chemical Property of (4S,5R)-2,2-diethyl 4-methyl 4-(4-bromo-2-nitrophenyl)-5-phenylpyrrolidine-2,2,4-tricarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-2,2-diethyl 4-methyl 4-(4-bromo-2-nitrophenyl)-5-phenylpyrrolidine-2,2,4-tricarboxylate

There total 3 articles about (4S,5R)-2,2-diethyl 4-methyl 4-(4-bromo-2-nitrophenyl)-5-phenylpyrrolidine-2,2,4-tricarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

aminomalonic acid diethyl ester (6829-40-9) + methyl 2-(4-bromo-2-nitrophenyl)acrylate (1202765-70-5) + benzaldehyde (100-52-7) → (4S,5R)-2,2-diethyl 4-methyl 4-(4-bromo-2-nitrophenyl)-5-phenylpyrrolidine-2,2,4-tricarboxylate (1291104-18-1)

Guidance literature:

With C₄₂H₂₈O₉P₂; In toluene; at 30 ℃; for 72h; optical yield given as %ee; enantioselective reaction; Molecular sieve;

DOI:10.1021/ol200652j

Reference yield:

4-Bromo-1-fluoro-2-nitrobenzene (364-73-8) → (4S,5R)-2,2-diethyl 4-methyl 4-(4-bromo-2-nitrophenyl)-5-phenylpyrrolidine-2,2,4-tricarboxylate (1291104-18-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.17 h / 90 °C

1.2: 2 h / 90 °C

2.1: formaldehyd; potassium carbonate / water / 2 h / 60 °C

3.1: C₄₂H₂₈O₉P₂ / toluene / 72 h / 30 °C / Molecular sieve

With formaldehyd; C₄₂H₂₈O₉P₂; potassium tert-butylate; potassium carbonate; In water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol200652j

Reference yield:

2-(4-bromo-2-nitro-phenyl)malonic acid dimethyl ester (100487-81-8) → (4S,5R)-2,2-diethyl 4-methyl 4-(4-bromo-2-nitrophenyl)-5-phenylpyrrolidine-2,2,4-tricarboxylate (1291104-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: formaldehyd; potassium carbonate / water / 2 h / 60 °C

2: C₄₂H₂₈O₉P₂ / toluene / 72 h / 30 °C / Molecular sieve

With formaldehyd; C₄₂H₂₈O₉P₂; potassium carbonate; In water; toluene;

DOI:10.1021/ol200652j

upstream raw materials:

aminomalonic acid diethyl ester

methyl 2-(4-bromo-2-nitrophenyl)acrylate

benzaldehyde

4-Bromo-1-fluoro-2-nitrobenzene